Holiday Homes in Peekskill

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Check prices for these dates

Our top choices for Peekskill holiday homes

1. Contemporary Cozy Cottage

Contemporary Cozy Cottage
Lake Peekskill
9.8 out of 10, Exceptional, (43 reviews)
"We’ve actually stayed here twice so that should tell you we enjoy the space and the host is lovely."
United States
Heather M.
The price is €366
includes taxes & fees
16 Nov - 17 Nov
Contemporary Cozy Cottage

2. 3BR West Point Retreat-3min to Back Gate+ King Bed

3BR West Point Retreat-3min to Back Gate+ King Bed
Highland Falls
8.4 out of 10, Very good, (7 reviews)
"Space was excellent, the multiple bedrooms with the extra bathroom was great. Kitchen was stocked with utensils, bathrooms were clean, living space was comfortable and cozy."
United States
Christine T.
3BR West Point Retreat-3min to Back Gate+ King Bed

3. Spacious 4-bedroom house in northern Westchester with sweeping views

Spacious 4-bedroom house in northern Westchester with sweeping views
Montrose
The price is €551
includes taxes & fees
13 Nov - 14 Nov
Spacious 4-bedroom house in northern Westchester with sweeping views

4. Lovely 3BR Home with parking-Walk to WP Gate!

Lovely 3BR Home with parking-Walk to WP Gate!
Highland Falls
10.0 out of 10, Exceptional, (7 reviews)
"Lovely home, great location and space for my family to have privacy. Enjoyed the deck for morning coffee. Would book again. "
United States
Briana T.
The price is €322
includes taxes & fees
17 Nov - 18 Nov
Lovely 3BR Home with parking-Walk to WP Gate!

5. Fabulous 3bdrm Home w/parking!

Fabulous 3bdrm Home w/parking!
Highland Falls
9.4 out of 10, Exceptional, (12 reviews)
"House was exactly as described. Would stay again."
United States
Beth M.
The price is €327
includes taxes & fees
8 Dec - 9 Dec
Fabulous 3bdrm Home w/parking!

6. Perfect 2BR with Free Parking! Walk to West Point!

Perfect 2BR with Free Parking! Walk to West Point!
Highland Falls
The price is €301
includes taxes & fees
17 Nov - 18 Nov
Perfect 2BR with Free Parking! Walk to West Point!

7. Lakefront Escape • Sauna • 1 Hr from NYC• 3 spacious bedrooms

Lakefront Escape • Sauna • 1 Hr from NYC• 3 spacious bedrooms
Lake Peekskill
8.0 out of 10, Very good, (3 reviews)
"This home was just as advertised and perfect for a girls weekend getaway. It was clean, cozy and a picture-perfect fall view. Would highly recommend."
United States
Karen W.
The price is €611
includes taxes & fees
17 Nov - 18 Nov
Lakefront Escape • Sauna • 1 Hr from NYC• 3 spacious bedrooms

8. Hudson Valley/West Point Retreat w/ parking!

Hudson Valley/West Point Retreat w/ parking!
Highland Falls
The price is €436
includes taxes & fees
17 Nov - 18 Nov
Hudson Valley/West Point Retreat w/ parking!

9. 3BR Home with Fireplace & Hudson Valley views near Woodbury Commons, West Point

3BR Home with Fireplace & Hudson Valley views near Woodbury Commons, West Point
Cornwall
10.0 out of 10, Exceptional, (16 reviews)
"Everything you could ask for!!"
United States
Elisabeth
The price is €398
includes taxes & fees
16 Nov - 17 Nov
3BR Home with Fireplace & Hudson Valley views near Woodbury Commons, West Point

10. Castle Retreat w/ Pool, BBQ, Game Room & Pets OK!

Castle Retreat w/ Pool, BBQ, Game Room & Pets OK!
Ossining
8.8 out of 10, Excellent, (10 reviews)
"It's an elegant older house with lots of room for company. Family friendly. The pool was great. My family enjoyed it."
United States
Karen O.
The price is €682
includes taxes & fees
16 Nov - 17 Nov
Castle Retreat w/ Pool, BBQ, Game Room & Pets OK!

11. Bright Cornwall-On-Hudson Vacation Rental!

Bright Cornwall-On-Hudson Vacation Rental!
Cornwall-On-Hudson
10.0 out of 10, Exceptional, (35 reviews)
"Very comfortable house and great location."
United States
Betty B.
The price is €607
includes taxes & fees
22 Nov - 23 Nov
Bright Cornwall-On-Hudson Vacation Rental!

12. Cozy 1845 Chapel Escape near Appalachian Trail and Fahnestock Park

Cozy 1845 Chapel Escape near Appalachian Trail and Fahnestock Park
Hopewell Junction
9.4 out of 10, Exceptional, (13 reviews)
"Lovely space and situation, unique. Close to the AT, as well."
United States
Peter W.
The price is €233
includes taxes & fees
13 Nov - 14 Nov
Cozy 1845 Chapel Escape near Appalachian Trail and Fahnestock Park

13. Summer Pool Oasis Custom Bar Arcade Pool Table

Summer Pool Oasis Custom Bar Arcade Pool Table
2.0 star property
Ossining
The price is €944
includes taxes & fees
16 Nov - 17 Nov
Summer Pool Oasis Custom Bar Arcade Pool Table

14. NEW! Cozy 3BR Home Near West Point & Hudson Valley - King Bed

NEW! Cozy 3BR Home Near West Point & Hudson Valley - King Bed
New Windsor
The price is €468
includes taxes & fees
1 Dec - 2 Dec
NEW! Cozy 3BR Home Near West Point & Hudson Valley - King Bed

15. Lux Bungalow on Gorgeous Lake. Relax. Explore nearby towns. Ski. Kayak. Hike.

Lux Bungalow on Gorgeous Lake. Relax. Explore nearby towns. Ski. Kayak. Hike.
Carmel Hamlet
10.0 out of 10, Exceptional, (21 reviews)
"Beautiful house. Great location and awesome hosts!"
United States
Robert T.
The price is €329
includes taxes & fees
15 Nov - 16 Nov
Lux Bungalow on Gorgeous Lake. Relax. Explore nearby towns. Ski. Kayak. Hike.

16. Lakefront • 7BR Retreat • Sleeps 12 • Massage Chair

Lakefront • 7BR Retreat • Sleeps 12 • Massage Chair
Monroe
10.0 out of 10, Exceptional, (5 reviews)
"The combination of an antique, old-style house with a modernized interior featuring all the amenities you could dream of made for an enjoyable and cozy experience. The house is located right at the back of the lake in a quiet neighborhood and comes fully equipped with:- A spacious layout- High-speed Wi-Fi- Useful massage chair - Fun recreational areas- Lovely decorThis house will truly become a staple in the area."
United States
Moshe F.
The price is €992
includes taxes & fees
15 Nov - 16 Nov
Lakefront • 7BR Retreat • Sleeps 12 • Massage Chair

17. Chestnut on Willow Lake

Chestnut on Willow Lake
Fishkill
9.8 out of 10, Exceptional, (6 reviews)
"Our family enjoyed a relaxing weekend before R-day at West Point and it was perfect! A beautiful property and we hope to be back another time!"
United States
Quintina R.
The price is €467
includes taxes & fees
13 Nov - 14 Nov
Chestnut on Willow Lake

18. Hudson View Hot Tub · Walk to Waterfront

Hudson View Hot Tub · Walk to Waterfront
Newburgh
10.0 out of 10, Exceptional, (1 review)
"The home has recently been renovated and it is very well presented with luxury furnishings and an excellently stocked kitchen. Views are amazing over the Hudson towards Beacon."
United States
Rachel M.
The price is €723
includes taxes & fees
15 Nov - 16 Nov
Hudson View Hot Tub · Walk to Waterfront

19. Lakefront Paradise Pool + Paddle Boats Sleeps 12

Lakefront Paradise Pool + Paddle Boats Sleeps 12
Monroe
10.0 out of 10, Exceptional, (5 reviews)
"We had a wonderful week long stay. The house is beautiful and right on the lake, with beautiful views and sunsetsWe were there for a West Point Graduation and was about a 30 minute drive to the school, even on the busy days of the parade and graduation dayThe house had plenty of room for our group and the host was easy to get ahold of. There are 4 official bedroom and 4 bathrooms and a basement and 2 office/den, 2 washer and dryers - one in the top floor and another in the basement which has...
United States
Courtney D.
The price is €1,224
includes taxes & fees
8 Dec - 9 Dec
Lakefront Paradise Pool + Paddle Boats Sleeps 12

20. Amazing Home Near West Point, Shopping, Skiing and Legoland

Amazing Home Near West Point, Shopping, Skiing and Legoland
Monroe
9.8 out of 10, Exceptional, (17 reviews)
"Very nice property in a nice neighborhood . Had all the amenities we needed and Ruth was super responsive. If we are in the area again, we will def stay at this location. "
United States
Kimberly R.
The price is €630
includes taxes & fees
21 Nov - 22 Nov
Amazing Home Near West Point, Shopping, Skiing and Legoland
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Learn more about Peekskill

Stroll along the scenic Hudson River waterfront where art galleries and craft breweries have transformed former industrial spaces. Take a guided tour of historic downtown's colourful murals or catch a performance at the beautifully restored Paramount Theatre.

A calm river with mountains on either side and a sunset sky.